Diethylamine → HCID 19594913, compound

HRID 612605Notes

Reaction equation

HRID 612605 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([C:21](O)=[O:22])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[O:19][CH3:20])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>C(Cl)Cl>[CH2:28]([N:30]([CH2:31][CH3:32])[C:21]([C:9]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=[CH:7][CH:8]=1)=[O:22])[CH3:29]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 19594776HCID 19594776, compound

Product 1

HCID 19594913HCID 19594913, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepare a stirred solution of 6-isopropoxy-2',4'-dimethoxy-biphenyl-2-carboxylic acid (8.60 g, 0.0276 mole) in CH2Cl2 (200 mL) at ambient temperature under argon. Dropwise add thionyl chloride (4.6 g, 54 mmol, 2.8 mL). Continue stirring for about 60 minutes. Cool the reaction to 0° C. and dropwise add diethylamine (19.7 g, 28 mL, 0.27 mole), ensuring the temperature does not rise above 25° C. Continue stirring the reaction for about 30 minutes after addition is complete. Wash the organic layer with water, separate, and wash twice with 100 mL 5% sodium bicarbonate. Separate again, wash with brine (sat'd NaCl) and dry over magnesium sulfate. Filter through celite and condense on a rotovap to give a viscous light brown liquid. Dissolve (partially) in methylene chloride (20 mL) and filter. Flash chromatograph, in 30% ethyl acetate/70% hexane, to remove a solid impurity which is discarded. Continue eluting to obtain a mixture of the discardable and desired product. Further chromatography isolates the title compound as a pale yellow liquid (6.80 g, 68%). (EtOAc/hexane 30:70; Rf =0.15).

Workup

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. customdoes not rise above 25° C
  4. stirringContinue stirring
  5. customthe reaction for about 30 minutes
  6. additionafter addition
  7. washWash the organic layer with water
  8. customseparate
  9. washwash twice with 100 mL 5% sodium bicarbonate
  10. customSeparate again
  11. washwash with brine (sat'd NaCl)
  12. dry with materialdry over magnesium sulfate
  13. filtrationFilter through celite and condense on a rotovap
  14. customto give a viscous light brown liquid
  15. filtrationfilter
  16. customFlash chromatograph, in 30% ethyl acetate/70% hexane, to remove a solid impurity which
  17. washContinue eluting
  18. customto obtain

Sources & evidence

ORD record
ord-c31d1639b6ae41e788c54aec39e706ba
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

Loading…